Process for dyeing cellulose-acetate threads



dyestuffs of the above given general formula lulose acetate threads dyed with our new dye stuffs and zene and 1- cellulose acetate Patented July 15, 1930 UNITED STATESIPATEIN'T', oF

osKAR SPENGLER, or nnanmmnunnemsnane,

GERMANY, ASSIGNORS, BYJIESNE ASSIGNMENTS, TO GENERAL 11m, on NEW YORK, N. YY., A CORPORATION or DELAWARE ICE PROCESS FOR DYEING CEI Iil'l'LOSE-ACETATE THREADS No Drawing". Application filed August 14, 1926, Serial No. males, and in Germany August 15, 1925.

"The present invention relates to the unsulfonated azo dyestuffs of the general formula:

uocugcn oau ux 3 wherein R represents a radicle of the benzene series which may 'befurther substituted and X the .radicle of an aromatic azo component. ur invention relates furthermore to the cel I Example 2.'The dye made from 1-,8 hydro xyethoxy-2- diazobenzene. and l-hydroxy- Water and in this solution cellulose acetate silk is dyed at -70 C Some sodiumsulphate may be added. Strong yellow tints are obtained. q

Example 3.-The dye made from l-fl-hydroxyethoxy 2 chloro 4 diazobenzene and l phenyl 3 methyl-5-pyrazolone ground with equal quantitiesof soap solu tion 1:10 and Turkey red oil. Cellulose acetate silk is dyed at 60-70 C. a strong clear ,yellow dyeing being obtained. are extraordinarily;adapted for the .dye ng I th Same'way th d m d f 1- 3- of cellulose acetate threads from an aqueous hydroxyethoxy; 4 2 diazobenzene medium. The dyeings thus produced are very strong and fast, while the corresponding dyes derived from diazotized amino-compounds or amino-ethoXy-c0mpounds are not adapted for dyeing cellulose-acetate threads. Our new dyestuffs may be obtained by com-- bining a ,8-hydroXy-ethoxy-diazo compound of the benzene series with matic azo component.

The following examples serve to illustrate our invention without limiting it thereto: Example 1.-The,dye made from 1-,8-hydroxyethoxy-4-d1azobenzene and aceto-acetic ponent. acid anilid having the probable formula: 2. In a process for dyeing cellulose acetate is well ground with the same quantity of soap and Turkey red oil. Cellulose acetate. silk to the material is dyed'at 60-70 C in an aqueous suspension of this mixture, a clear greenish yellow being obtained. Iii the same manner the dye P made from l-,8-hydr0XyethoXy-4c-dyazobenamino 7 -hydroxynapthalene produces a dark claret dyeing. The dyemade from 1 B hydroxyethoxy 4 diazobenzene which may be substituted or not. and 2- amino-7--hydroxynaphthalene dyes- I 3. In a process for dyeing cellulose acesilk brownish red-orange; tate threads the step which consists in apf'rom l-fl-hydroxyethoxy-Q- plying to the material in an aqueous medium diazobenzene and 2 hydroxynaphthalene the unsulfonated azo dyestuft' of the probgives very clear intensive red shades. able formula:

noon. OHLOON= Orraooomooom to a process for dyeing cellulose acetate threads byaneans of our new dye stuffs. I

WV e have found that the unsulfonated azo silk yellow.

What we claim is: 1. In a process for dyeing cellulose acetate threads the step which consists in applying any suitable aro- R represents a radicle of the benzene series,

resents the radicle of an aromatic azo comgroup and represents an aromatic nucleus of the benzene 0r naphthaleneserles,

dyestutf of the general for-.

and "1,3-dioxybenzene dyes cellulose acetate which may be further substituted and X rep- I the probable formula:

noon-.omoO- =NONHoocmooon,

4. As new products the unsulfonated azo dyestufisof the general formula:

wherein R represents a radicle of the benzene series, which may be further substituted, and X represents the radicle of an aromatic azo component.

5. As new products the unsulfonated azo dyestuffs ofcthe general formula:

wherein R represents a radicle of the benzene series which may be substituted by a halogen or a. nitro grou and X represents an aromatic nucleus 0 the benzene or naphthalene series,v which may be substituted or not.

6. As a new product the azo dyestufl of which dyes cellulose acetate silk clear greenish ellow shades. y a 7 Cellulose acetate silk dyed with the dye-- stufis described in claim 4. 1 8. Cellulose acetate silk dyed with the dyestufis described in claim 5. r a

9. Cellulose acetate silk dyed with the dyestufi described-inclaim 6. I 1 In testimony whereof we aflix our signatures.

- OSKAR SPENGLER; I WERNER MULLER. 

